반응 #2844

반응 방정식

(5-iodo-thiophene-3-yl)methanol

DMF

→

title compound

4-Hydroxymethyl-thiophene-2-carbonitrile

용매

EtOAc

반응 조건

후처리

1. 1
   세척The resulting solution is washed with 1N NH4OH, H2O and sat. NaCl
2. 2
   건조The organic layer is dried over MgSO4
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타The crude product is purified by column chromatography
6. 6
   세척eluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

실험 절차

To a solution of (5-iodo-thiophene-3-yl)methanol (42 g, 176 mmol) in 150 mL of DMF is added zinc cyanide (12.4 g, 106 mmol) and tetrakis(triphenylphospine)palladium (0) (8.13 g, 7.04 mmol). The solution is heated to 80° C. After 6 h, the solution is diluted with 3 L of EtOAc. The resulting solution is washed with 1N NH4OH, H2O and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (10 g, 72 mmol) as a clear oil.

출처